sodium acetate; pyridinium chlorochromate in dichloromethane T=10°C; 2.5 h;

1: 1.) O2, rose bengal, 2.) 15 percent aq. Na2SO3 / 1.) methanol, irradiation, 7 h, 2.) methanol, 15 h 2: 68 percent / manganese dioxide / petroleum ether / 3 h View Scheme

1: 1.) diisopropylamine, n-butyllithium, / 1.) ether, 1 h, 2.) ether, overnight, 3.) reflux, 3 h 2: 80 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 2.5 h / 10 °C View Scheme

hydrogen; palladium on activated charcoal in ethanol 0.583333 h;